I had to take my shoes off to climb onto the first wooden boat. I’d never been to a yacht club before, but it conjured images of very swanky dresses and brightly colored cocktails, so I showed up at the reception for the 30th annual McNish Classic Yacht Race in heels, which it turned out were a big mistake for wooden boats. Some of the captains had gone to great lengths to make sure their wooden floor beams were authentic, as well as lovingly varnished for race day, and my heels would scratch them up. I spent most of the evening touring the boats barefoot, which ended up being the perfect way to do it.

The floor boards of teak and holly beneath my feet were just one example of the tender care the owners of these boats give their old gals. Graem Elliot, co-owner of the Raiatea, a 43-foot sloop from Long Beach, commented that owning a classic wooden yacht is like “owning a really large piece of old furniture.” With each boat in the regatta designed before 1952, the fun is in the restoration, the laborious weekends spent spit-shining the mast, the search for the perfectly authentic compass or cabin lantern. Owning a wooden boat, according to Dick McNish, founder of the race, is a labor of love.

“It’s like working on the Golden Gate Bridge,” McNish says. “You start at one end and work your way to the other. Then, you turn around and go back.” Many of the other captains reiterated this idea: All a wooden boat owner sees when he looks at his vessel is the next project.

Even when pointing out to me all the little improvements they hope to make on their boats, the owners were careful to point out that it is the work they treasure; the constant labor makes a classic wooden yacht the most rewarding type of boat. Wooden boats have a history tucked inside the grains of their floor boards, and the owners seek only to highlight that history, to bring another time back to life for an afternoon, to remind themselves and the race’s audience of an era of boating before Fiberglas and high-speed motors.

“These are time machine boats,” says Jon Duff, co-owner of the Raiatea. “The moment you step on board, you are transported back.”

Finding common waters

The view of the horizon on race day showed me just what they meant. I sat on the white helm of the power boat the press was cordoned to, at the starting line, miles out from the harbor, and watched the magnificent vessels float gracefully along with the wind. Their massive sails in all shades from pure white — McNish got brand new sails just for this year’s race — to worn gold puffed out without a wrinkle, as if they were stable, structured things. I was surrounded by these historic creatures, dipping and curving into the wind, waiting patiently for their start time. We watched with bated breath as a crew member of the Bequia climb the mast. The boat rocked with the waves, but he remained steady, harnessed in, a testament to the skill the crew put in to sailing these ships. Watching them race is a reminder of the time they have not forgotten — a time when everyone who owned a boat built her himself, and knew how to sail her, too.

“Out here,” McNish says, “keeping up these wooden boats, working hard, we all have a common bond.”

Indeed, despite their different walks of life, the captains all have something in common when they take their vessels to the open seas. In fact, it’s an entirely different life for most of them. Most of these captains are not captains full time; the McNish is a vacation weekend for them, and their boat is their way of escaping the daily grind. Internet technology managers, auto parts manufacturers, quality control specialists and even teachers steer the antique wheels and man the helms, and maintaining the other-world isolation of their boat is their retreat.

All this is to say that, race or no race, these salty dogs are in town to have a good time — to get away for a weekend, to show off their hard work, to demonstrate the level of skill necessary to race a classic wooden yacht, and to laugh. The crew of the Spitfire raced with Scottish hats, red wigs attached to the bottom, bagpipe music blaring. The party lasts all weekend.

History on parade

The McNish race was founded on the idea that classic wooden yachts and their crew have a character all their own, from a different time, one that deserves to be honored. McNish has, over the years, developed a handicap formula and staggered the start times so most of the boats cross the finish line at the same time, a demonstration more like a parade at an antique car show than a highly contested speedboat race. The 17-mile triangular course was designed so all skippers, even those with only basic sailing knowledge, can be competitive. And McNish gives out awards to nearly every boat in the competition, for honors ranging from least elapsed time to most distant port, as well as first, second and third place in each category of boat.

But the beloved Strathmore Cup, given to the first to cross the finish line (this year, the Elusive II from Ventura, skippered by Don Greene), is a prize truly exemplary of the spirit of the race: the skipper’s weight in Mumm’s champagne.

McNish speaks of the race, and of his boat, the Cheerio II, with such quiet passion, it’s difficult to believe he will retire from the race after this year. This is the race’s 30th year, and McNish, at age 80, still plans to captain his boat in the years to come, but he is happy to step down and leave the legacy of the McNish Classic Yacht Race behind him. “I started this race so we’d have a place for these boats,” he says. “I just wanted to get all these old gals together.”

The fatherly protection and pride with which the captains speak of their boats shows they all have similar reasons for choosing to race classic wooden boats rather than power boats or modern sailboats. They treasure the challenge, the history and the escape from the harried contemporary world. Friday night, while we sat sipping mai tais on the deck of the Sparrow, a small motorboat chugged by, with an older man at the helm and his bleached blond wife sipping a glass of chardonnay. She yelled out to us on the teak and holly deck: “Too high maintenance!” The crew all laughed, and commented how that was all anybody else saw when they looked at a wooden boat; strange to them, given that it is the hard work they love about their vessels.

Elliot smirked, glad to get a shot back at those living the cushy modern life in a motorboat: “Actually,” he said, “I think she was talking about herself.”